1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

HCID 1388

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Basic information

CAS: 28289-54-5
Standard SMILES: CN1CC=C(c2ccccc2)CC1
InChIKey: PLRACCBDVIHHLZ-UHFFFAOYSA-N
Molecular formula: C12H15N
Average molar mass: 173.259 g/mol
Monoisotopic mass: 173.12044948

Names & identifiers

Preferred name: 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
IUPAC: 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
English name: 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Molecular formula: C12H15N
Molecular weight: 173.25

Names & synonyms

MPTPNSC 139654Naphthoic Acid Impurity 1111-METHYL-4-PHENYL-PIPERIDINE-3-EN1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridin1,2,3,6-tetrahydro-1-methyl-4-phenylpyridine1,2,3,6-tetrahydro-1-methyl-4-phenyl-pyridin1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROXPYRIDINE1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDRO-PYRIDINEN-METHYL-4-PHENYL-1,2,3,6-TETRAHYDRO-PYRIDINE

Database identifiers

CAS: 28289-54-5
PubChem CID: 1388
DTXSID: DTXSID8040933
ChEMBL: CHEMBL24172
ChEBI: CHEBI:17963
UNII: 9P21XSP91P
EC Number: 248-939-7
Nikkaji: J22.909A

Properties

Physicochemical properties

Melting point: 36 °C · aprox. 36°C
Boiling point: 128 · 128-132 °C12 mm Hg(lit.)
Density: 1.001 · 1.001±0.06 g/cm3(Predicted)
storage temp.: Inert atmosphere,Room Temperature
solubility: Chloroform (Slightly), Dichloromethane (Slightly), Ethyl Acetate (Slightly)
pka: 8.66 · 8.66±0.40(Predicted)
form: Solid
color: Pale Yellow to Light Yellow
Merck: 13 · 13,6319
Stability: Stable. Incompatible with strong oxidizing agents.
FDA UNII: 9 P21XSP91P · 9P21XSP91P
Symbol(GHS): 8 · GHS08,GHS06
Signal word: Danger
Hazard statements: 370 · H370-H301
Precautionary statements: 264 · P264-P270-P301+P310-P321-P330-P405-P501-P260-P264-P270-P307+P311-P321-P405-P501
Hazard Codes: T
Risk Statements: 25 · 25-39/23/24/25
Safety Statements: 45 · 45
RIDADR: 2811 · UN 2811 6.1/PG 2
WGK Germany: 3 · 3
RTECS: 8358900 · UT8358900
HazardClass: 6.1 · 6.1(b)
PackingGroup: III
Hazardous Substances Data: 28289 · 28289-54-5(Hazardous Substances Data)
Toxicity: 1 · Human toxicity originally discovered when it was an unexpected by-product from the illicit synthesis of a heroin substitute (i.e., meperidine analog). Currently used experimentally as the primary animal model for the study of Parkinson’s disease. MPTP is a neurotoxicant that is activated to 1-methyl-4-phenylpyridinium ion (MPP1) by the actions of monoamine oxidase B located in the mitochondria of brain astrocytes. The MPP1 is then transported into dopamine, and to a lesser extent, other monoaminergic neurons. Once inside these dopamine neurons in the substantia nigra, it destroys these neurons by mechanisms that may involve an oxidative cascade and/or inhibition of electron transport. Intoxication causes a parkinsonism syndrome almost identical in signs and symptoms to Parkinson’s disease, including rigidity, bradykinesia, tremor, and postural instability. In the event of known ingestion, immediate (but not delayed) administration of a monoamine oxidase inhibitor (especially one selective for MAO-B like deprenyl) and dopamine uptake inhibitor can be therapeutic.

Safety & regulation

Safety data

wgk: 3
rtecs: UT8358900
ridadr: UN 2811 6.1/PG 2
Toxicity: Human toxicity originally discovered when it was an unexpected by-product from the illicit synthesis of a heroin substitute (i.e., meperidine analog). Currently used experimentally as the primary animal model for the study of Parkinson’s disease. MPTP is a neurotoxicant that is activated to 1-methyl-4-phenylpyridinium ion (MPP1) by the actions of monoamine oxidase B located in the mitochondria of brain astrocytes. The MPP1 is then transported into dopamine, and to a lesser extent, other monoaminergic neurons. Once inside these dopamine neurons in the substantia nigra, it destroys these neurons by mechanisms that may involve an oxidative cascade and/or inhibition of electron transport. Intoxication causes a parkinsonism syndrome almost identical in signs and symptoms to Parkinson’s disease, including rigidity, bradykinesia, tremor, and postural instability. In the event of known ingestion, immediate (but not delayed) administration of a monoamine oxidase inhibitor (especially one selective for MAO-B like deprenyl) and dopamine uptake inhibitor can be therapeutic.
risk_code: 25-39/23/24/25
Signal word: Danger
Symbol(GHS): GHS08,GHS06
hazard_code: T
safety_code: 45
hazard_class: 6.1(b)
packing_group: III
Hazard statements: H370-H301
Precautionary statements: P264-P270-P301+P310-P321-P330-P405-P501-P260-P264-P270-P307+P311-P321-P405-P501
Hazardous Substances Data: 28289-54-5(Hazardous Substances Data)

Chemistry & industry

Applications

Uses1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine is a dopaminergic neurotoxin that reportedly causes a severe and irreversible Parkinsonian condition in humans and monkeys.

Suppliers44 total

武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]

陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]

Aladdin Scientific[email protected]

Hangzhou IKSChem Technology Co., Limited13625816949 · [email protected]

武汉易泰科技有限公司上海分公司18930552037 · [email protected]

Additional notes

DefinitionChEBI: A tetrahydropyridine that is 1,2,3,6-tetrahydropyridine substituted by a methyl group at position 1 and a phenyl group at position 4.